Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A
Show others and affiliations
2012 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 32, 6504-6512 p.Article in journal (Refereed) Published
Abstract [en]

An important feature of the synthesis of salinosporamide A. a potent proteasome inhibitor, is the establishment of the quaternary stereocenter at C3. A new route has been developed based on the methylation of a functionalized pyrrolidinone. Direct methylation reaction led to the unwanted diastereomer: however, by means of a Corey-Chaykovsky reaction followed by LiAlH4 epoxide opening, the desired alcohol was obtained. The pyrrolidinone was elaborated through a key allylation reaction between a tertiary allyltitanium reagent and an aldehyde bearing a spiroketal moiety in alpha-position.

Place, publisher, year, edition, pages
2012. Vol. 68, no 32, 6504-6512 p.
Keyword [en]
Salinosporamide, Hoppe allylation, Pyrrolidinone, Methylation reaction, Corey-Chaykovsky reaction
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-80630DOI: 10.1016/j.tet.2012.05.103ISI: 000306267800014OAI: oai:DiVA.org:su-80630DiVA: diva2:556466
Funder
Swedish Research Council
Note

AuthorCount:10;

Available from: 2012-09-25 Created: 2012-09-25 Last updated: 2017-12-07Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Santoro, StefanoHimo, Fahmi
By organisation
Department of Organic Chemistry
In the same journal
Tetrahedron
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 48 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf